Fused naphthalenes

Abstract

The invention relates to fused naphthalenes of the general formula I, in which A 1 , A 2 , A 3 , A 4 , Q 1 -Q 2 , G 1 -G 2 , R 1 , R 2 , X 1 , X 2 , X 3 , X 4 , X 5 , Z 1 , Z 2 , Z 3 , Z 4 , q, r, s and t have the meaning indicated, and to the use thereof as components of liquid-crystalline media and to an electro-optical display element containing them.

1. A fused naphthalene of the formula I 
       
         
           
           
               
               
           
         
       
       in which
 A 1 ,A 2 ,A 3 ,A 4  each, independently of one another, denote a 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene radical which is unsubstituted or substituted by one to four F atoms and in which one or two CH 2  groups may each, independently of one another, be replaced by —O— or —S— in such a way that heteroatoms are not linked directly to one another, a 1,4-phenylene radical, which may be substituted by one or two fluorine or chlorine atoms and in which, in addition, one or two CH groups may be replaced by N, or denote a 1,4-bicyclo[2.2.2]octylene radical or a 2,6-spiro[3.3]heptylene radical, 
 Q 1 -Q 2  denotes O—CH 2 , or O—CF 2 , 
 G 1 -G 2  denotes CH 2 —CH, CF 2 —CH, CH═C, CF═C, 
 R 1 ,R 2  each, independently of one another, denote an alkyl radical having 1 to 12 C atoms which is unsubstituted or at least monosubstituted by halogen and in which one or more non-adjacent CH 2  groups may each, independently of one another, be replaced by —O—, —S—, —CO—, two adjacent CH 2  groups may each be replaced by —CH═CH—, —CF═CF—, —COO—, —OOC—, —C≡C—, a 1,2-cyclopropanylene radical, which may also be substituted by two F atoms, or three adjacent CH 2  groups may be replaced by a 1,3-cyclobutanylene radical, which may also be substituted by two F atoms, or denote F, Cl, —OCF 3 , —OCHF 2 , —CN, —NCS or H, with the proviso that either only R 1  or only R 2  can be H, 
 X 1 ,X 2 ,X 3 , 
 X 4 ,X 5  each, independently of one another, denote H, F or Cl, 
 Z 1 ,Z 2 ,Z 3 ,Z 4  each, independently of one another, denote the single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CH 2 CHF—, —CHFCH 2 —, —CF 2 O—, —OCF 2 —, —COO—, —OOC—, —CH═CH—, —CF═CF—, —C≡C—, and 
 q,r,s,t each, independently of one another, denote 0 or 1. 
 
     
     
       2. The fused naphthalene according to  claim 1 , wherein Q1-Q2 has the meaning O—CH 2 . 
     
     
       3. The fused naphthalene according to  claim 1 , wherein Q 1 -Q 2  has the meaning O—CF 2 . 
     
     
       4. The fused naphthalene according to  claim 1  of the formula 
       
         
           
           
               
               
           
         
       
       in which R 1 , R 2 , q and s have the meaning indicated. 
     
     
       5. The fused naphthalene according to  claim 1  of the formula 
       
         
           
           
               
               
           
         
       
       in which R 1 , R 2 , q and s have the meaning indicated. 
     
     
       6. A method of using compounds of the formula I according to  claim 1  comprising employing said compounds as components of liquid-crystalline media. 
     
     
       7. A liquid-crystalline medium having at least two liquid-crystalline components, comprising at least one compound according to  claim 1 . 
     
     
       8. An electro-optical display element, comprising a liquid-crystalline medium according to  claim 7 . 
     
     
       9. A fused naphthalene of formula I 
       
         
           
           
               
               
           
         
       
       in which
 A 1 ,A 2 ,A 3 ,A 4  each, independently of one another, denote a 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene radical which is unsubstituted or substituted by one to four F atoms and in which one or two CH 2  groups may each, independently of one another, be replaced by —O— or —S— in such a way that heteroatoms are not linked directly to one another, a 1,4-phenylene radical, which may be substituted by one or two fluorine or chlorine atoms and in which, in addition, one or two CH groups may be replaced by N, or denote a 1,4-bicyclo[2.2.2]octylene radical or a 2,6-spiro[3.3]heptylene radical, 
 Q 1 -Q 2  denotes O—CH 2 , CH 2 —O, O—CF 2 , CF 2 —O, CH 2 —CH 2 , S—CF 2 , CF 2 —S, O—CO or CO—O, 
 G 1 -G 2  denotes CH 2 —CH, CF 2 —CH, CH═C, CF═C, 
 R 1 ,R 2  each, independently of one another, denote an alkyl radical having 1 to 12 C atoms which is unsubstituted or at least monosubstituted by halogen and in which one or more non-adjacent CH 2  groups may each, independently of one another, be replaced by —O—, —S—, —CO—, two adjacent CH 2  groups may each be replaced by —CH═CH—, —CF═CF—, —COO—, —OOC—, —C≡C—, a 1,2-cyclopropanylene radical, which may also be substituted by two F atoms, or three adjacent CH 2  groups may be replaced by a 1,3-cyclobutanylene radical, which may also be substituted by two F atoms, 
 X 1  and X 2 , are F, 
 X 3 , X 4  and X 5  are H 
 Z 1 ,Z 2 ,Z 3 ,Z 4  each, independently of one another, denote the single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —CH 2 CF 2 —, —CF 2 CH 2 —, —CH 2 CHF—, —CHFCH 2 —, —CF 2 O—, —OCF 2 —, —COO—, —OOC—, —CH═CH—, —CF═CF—, —C≡C—, and 
 q,r,s,t each, independently of one another, denote 0 or 1.